An Inside Look At Startup Weekend

My name is Rachel Hyman, and I’m with a startup called Edit Huddle. We recently competed in Chicago Startup Weekend. I entered the competition on Friday night with essentially zero experience, not entirely sure of what I was getting myself into. I had mentioned my weekend plans to a few friends, and the common response was “How’d you get involved with that?”

I was still trying to answer that question as I walked up to Excelerate Labs in the early evening on Friday. My best answer is that I’d been having a creeping fear of ending up in a dead-end job post-graduation, miserable and stagnant in order to pay the rent. I was feeling like my ambition outpaced what I was doing in my life, and I wanted to get involved in creative, challenging, self-motivated work with other young people. I had gotten some secondhand exposure to the world of entrepreneurship and startups, and figured Startup Weekend was a good place to get a real taste of this world.

Day 1: Friday

Before the event officially started, people mingled over pizza and bounced their ideas off one another, a pre-pitch of sorts. After a brief introduction, the real pitches began, with each person given 60 seconds. We heard 64 ideas, according to my notes from that weekend. The pitch time was great for getting everyone psyched up, because all the pitch-ers came out full of enthusiasm to convince us of their ideas’ greatness.

As I kept circling the room with my tickets, I ran into some guys with an idea for a blog-editing tool called Edit Huddle. Essentially, blog readers highlight a selection of text, pick the type of error (spelling, grammar, factual, etc.), and the information gets sent directly to the blogger, who can rectify the mistake. I raised some criticism of their idea at first. Then their developer Mark drew an analogy toSoundCloud, which lets users comment on specific points in a song, to show me the potential power of their tool—it could be used for collaborative essay editing or commenting on a specific blog paragraph. I was sold. And that’s how I ended up working with Edit Huddle. The top 13 ideas that were given the most tickets made the first cut. Teams were quickly formed, and then the real work began.

We staked out a corner conference room with a great view, then talked over our preliminary plan for the weekend. There were a lot of tasks on the list: develop a working demo, prove customer validation, put together a pitch for Sunday, design a new website, and so on. One of the things I loved is that even though we all had a ton to accomplish, we didn’t immediately split off into our individual jobs. We drew a mockup of the dashboard (the mechanism for bloggers to view and fix errors) up on the whiteboard, and talked the specifics of our idea out. Especially as a nontechnical person, I found that this initial group collaboration helped me find my footing and build cohesiveness with my team. I was tasked with marketing and social media, with customer validation being the first priority. Imran, the founder of Edit Huddle, had already done some research and determined that “mommy bloggers” were an ideal market to target. They post often, have a high degree of interaction with their readers, and naturally are often too busy to correct errors. I found an index of popular mommy blogs, and set to work compiling information and contacting them, asking them to take our short survey. Even though we had to leave the building by 11 pm, I stayed up until 3 am building up a list of mommy bloggers.

TAKEWAY #1: LEARN ON YOUR FEET

I came in to Startup Weekend with very little experience and no technical prowess. I was nervous about whether I even belonged there. But already by Friday night, I was picking up a ton of knowledge. Customer validation, MVP, pivoting, hockey stick growth, pain point: I was in the thick of all these terms and getting a firsthand understanding of what they meant. I listened to everybody, asked questions when I didn’t get something, and all around just threw myself into Startup Weekend. With force. The best way to learn is by doing, and though I often felt like I was stumbling in the dark, I at least got a feel for what was around me.

Day 2: Saturday

Saturday, as the only full day of work, was the most intense. Our team felt the pressure to make measured progress. One of the things that we did well over the weekend was pivoting. As evening approached on Saturday, we looked at the response rate of the mommy bloggers and determined that it wasn’t where it needed to be. We really needed to show that the tool was a viable product that fills a gap in the market. A big boost came when Seth Kravitz, one of the founders of Technori, responded to our email with positive feedback on Edit Huddle. Pivoting is a pretty accurate analogy for what we did after that point. We switched our strategy up, reaching out to people in the Chicago startup/entrepeneurial/tech world who might have an interest in Edit Huddle and be able to provide feedback. The Seth Kravitz quote went straight into our promotional materials and any emails we were sending out. And the pivot worked, because we got a great response rate from the Chicago crowd, including Entrepreneurs Unpluggd. Pivoting helped us build momentum; it was the kick in our pants that impelled us to keep “cranking” (that’s some in-house slang at Edit Huddle) through sleep deprivation. On my end, Saturday was all about extending our reach and getting the word out to as many people as possible: connecting with people on Facebook and Twitter, racking up survey responses, and finding beta testers.

TAKEAWAY #2: COLLABORATION, NOT COMPETITION

Continuing along the lines of my first takeaway, I learned a lot from my fellow participants in Startup Weekend. One of the reasons the event was such a positive experience was the atmosphere of incredible energy, excitement, and friendliness. It didn’t feel like too much of a competition, which is not to say we weren’t motivated to buckle down, but rather there was no cutthroat feeling or ill will in the building. Whenever I walked in to the kitchen to grab coffee (a frequent occurrence), I was struck by how genuinely friendly people were. Everyone was eager to hear about how other people’s projects were progressing, and people exchanged constructive criticism over the course of the weekend. When you’re spending 54 intense hours in bed with your own idea, it can be hard to see pitfalls of the strategy you’ve labored over. The other participants, as well as mentors like Neal Sales-Griffin of Code Academy and the organizers of Startup Weekend, helped widen that tunnel vision and focus our activities. The weekend was partially a huge networking event, in the best way possible. As Imran will tell you, I had apprehensions about the idea of networking, but Startup Weekend showed me how throwing a bunch of smart, motivated young people in a room can drive positive activity. Even though we were split up into teams, the weekend felt like more of a huge collaboration than a competition.

Day 3: Sunday

Sunday was the final push: the time to put the finishing touches on our demo, send out a last batch of emails and tweets, and put our pitch together. One of Neal’s big comments when he visited the Edit Huddle room on Saturday was that we had to start working on our pitch. We had been so focused on creating our product and validating it that we hadn’t been thinking about one of the big tasks of the weekend: putting together a killer pitch for the closing on Sunday. I kept forgetting that Startup Weekend really was a competition. We went over our progress since Friday: we had gotten a 17% response rate, and 85% of survey respondents said they’d use our tool. We also drew up a great example for our presentation, riffing on a big-name tech blog that seems especially prone to errors. Imran practiced making his pitch enthusiastic, personable, and most importantly, articulate.

Work stopped around 5:30, and the exhausted participants gathered in the main room for pitch time. Each team had five minutes to present, and then there were five minutes of questions from the judging panel. The judges’ comments were helpful especially for startups planning to continue beyond Startup Weekend, as they didn’t hesitate to raise objections and criticize revenue models.

I felt proud of all the progress we had made over Startup Weekend. We got a remarkable amount of traction over an intense 54 hours—during a non-workweek, no less—and regardless of what happened at the judging session, I’d deem the competition a success for Edit Huddle. The judges agreed on that much, and we were one of the winners at Startup Weekend. Even more exciting is the fact that Edit Huddle wasn’t contained in that competition. Our team had a four-hour work session the following Tuesday. We’re really launching this thing. Which brings me to…

TAKEAWAY #3: PUSH YOURSELF

Logically, I shouldn’t have even been in Startup Weekend. But I felt compelled to try something new out, and I basically fell into something great. And now I’m working with Edit Huddle. I feel excited about it everyday and I’m learning so much. An experienced entrepreneurial friend told me that it never stops feeling like you’re stumbling around in the dark. But it’s about finding good people to crash around with, and acting in spite of the fear of what’s ahead in the darkness. Am I a little scared? Yes. Am I totally thrilled anyway to forge on? You bet. Bring on the darkness.